


The Pizza Man

by supernatural9917



Category: Supernatural
Genre: But we all know there's only one ending, Castiel is the actual pizza man, Dean Winchester Wears Panties, Dean likes getting tied up, Dean likes pizza, Dean sleeps around a bit, Dom Castiel/Sub Dean Winchester, Fluff and Smut, Humor, Light Dom/sub, M/M, Pizza Man Anthology, Spanking
Language: English
Status: Completed
Published: 2020-01-14
Updated: 2020-01-14
Packaged: 2021-02-27 15:20:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,939
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22259350
Author URL: https://archiveofourown.org/users/supernatural9917/pseuds/supernatural9917
Summary: Gabriel needs a delivery guy for his pizza place. Cas needs some money and doesn't mind his brother owing him a favour. It's not all bad, though- there's free pizza, a uniform that brings out his eyes... oh, and a certain repeat customer with green eyes and a tendency to flirt with the pizza man despite always having a romantic guest over to share his order. Will Cas ever get to live out his pizza man porn fantasies?Yes, of course he will.
Relationships: Castiel/Dean Winchester, background Dean Winchester/Others
Comments: 16
Kudos: 426
Collections: The Pizzaman: A Destiel Anthology





	The Pizza Man

**Author's Note:**

  * For [foxymoley](https://archiveofourown.org/users/foxymoley/gifts).



> I was so happy to be part of the fantastic Pizza Man anthology, a book of classic porn tropes featuring our two favourite idiots, initiated and compiled by the always fabulous [Foxy](https://archiveofourown.org/users/foxymoley). I was particularly honoured to be invited to write the title piece, featuring header art by Foxy herself. I hope I did Dean and Cas, Foxy, my beta Athaclena, and Destiel smut lovers worldwide proud!

'Cassie, come on, I'm begging you,' Gabriel whined. 'Business is really taking off, and I'm desperate for delivery drivers. And it's not like you can't use the money, right?'

Castiel glared at his brother, briefly fantasising about shoving the bastard into his own pizza oven. Bringing up his money problems was a low blow and calling him by his second-most hated nickname (the worst was Asstiel, which their older brother Luke had used exactly once before getting punched right in the dick) only rubbed salt in the wound. 'Don't call me that,' he growled, and Gabriel put his hands up in surrender.

'OK! No problem! Hell, I won't call you that ever again if you help me. Just for a month, just to give me time to hire some more people.'

'Fine,' Castiel sighed before the puppy-dog eyes could come out. 'A month. And I get free pizza.'

'Of course! Thank you, thank you, thank you!' Gabriel reached under the counter and handed Castiel a blue polo shirt and baseball cap, both with the logo of Heavenly Pizzas: a cartoon version of Gabriel in a flowing white gown with fluffy white wings and a pizza instead of a halo. With a roll of his eyes, Castiel pushed the cap onto Gabriel's head.

'I'm not wearing the hat.' Without waiting for a reply, he stalked off to the bathroom to change into the polo shirt. By the time he came back, Gabriel had a stack of pizzas in insulated delivery bags and their respective order receipts. 

'I seriously owe you one, Cas!' With an enthusiastic hug, Gabriel sent Castiel on his way.

Castiel stacked the pizzas carefully in the back of his gold Lincoln Continental and made sure the hydraulics were off before starting the engine. Gabriel had put the deliveries in a logical geographical order to form a loop that started and ended at the pizzeria, so Castiel put the first address into his GPS and set off. The first few deliveries were uneventful- a middle-class family who tipped well, a grumpy old man who didn't, and a couple of college students who at least rounded up their bill. 

The last delivery was to an apartment a few blocks away from the restaurant, and Castiel expected it to be just as routine as the rest. Instead, the door was opened by a leggy blonde wearing nothing but a man's leather jacket.

'Um, hello,' Castiel said awkwardly. 'Pizza delivery.'

'Yummy!' the girl said before turning her head back. 'Dan! Pizza's here!'

'Jesus Christ, Candy!' came the responding shout. 'My name is Dean, and you need to untie me first!' Castiel's eyebrows shot up, though he wasn't even sure which part of that reply was the most intriguing. 

'Oh yeah, oopsie!' Candy giggled, running back to the bedroom. A moment later, a very handsome man, presumably Dean, came out tying up a robe and looking somewhat sheepish.

'Uh, sorry, man,' Dean said as he gave Castiel a handful of cash in exchange for the pizza.

'No problem. This has definitely been my most interesting delivery tonight.' Dean's smile emboldened something in Castiel, and he continued, 'A bit of advice, though: if someone doesn't even know your name, you probably shouldn't be letting them tie you up.'

Dean chuckled. 'You've got a point there.' He looked Castiel up and down and licked his lips. 'Totally unrelated, but what's _your_ name?' He waggled his eyebrows suggestively, and this time it was Castiel who laughed.

'Wouldn't you like to know?' he replied with a wink. 'Enjoy your pizza, Dean.'

**********

A week later, Castiel was back on the delivery route. There were a couple of repeat customers, and as he walked up the vaguely familiar walkway, he realised that one of them was Dean. He grinned to himself, wondering if Candy would open the door again while poor Dean was tied up in the bedroom. He rang the bell, and this time a pretty brunette answered. She was slightly more dressed than Candy had been, but that had been a pretty low bar.

'Hey, is that the pizza?' Castiel heard Dean shout from inside.

'Yeah!' the girl replied. 'I can get it.' She began to reach into her purse, but Dean quickly appeared at the door, wearing loose basketball shorts hanging low off his hips and no shirt.

'Hi,' he addressed Castiel with a flirtatious smile. 'How much do I owe ya?'

'Fifteen ninety-nine.'

Dean handed him a twenty and winked. 'Keep the change.'

'Thank you, Dean.' 

'Hey, you remembered!' Dean said, clearly pleased.

'Your name's Dean?' the brunette asked. 'I thought it was Dan.' She walked away with the pizza, missing the grimace on Dean's face.

'I hope you'll remember my advice from last week,' Castiel said with a raised eyebrow.

'No bondage with people who can't remember my name, I promise. Changing the subject completely, I don't suppose your shift is over soon?'

Castiel chuckled. 'I'm afraid I just started.'

'Too bad. Can I at least get your name?'

'Enjoy your pizza, Dean,' Castiel grinned as he walked away.

**********

Over the next three weeks, Castiel continued to deliver to Dean's apartment like clockwork every Saturday. Every Saturday, Dean would have a different busty beauty over, and he would playfully flirt with Castiel and try to find out his name. Castiel knew it didn't mean anything, but he enjoyed their brief interactions so much that he had continued to help Gabriel on Saturdays even after another delivery driver had been hired.

Tonight, there were two pizzas in Dean's order, and as Castiel walked up to the door, he wondered if Dean had managed to organise a threesome. Dean seemed like the type who would go for twins or something. Much to his surprise, when he knocked on the door, it was opened by a handsome, burly, bearded man. 

'Pizza's here, cher,' he called back to Dean as he pulled out his wallet. 'What do I owe you, chief?' 

'Um, twenty-two fifty,' Castiel replied, confused at the lack of sexy female date. Maybe Dean was having a buddy night or something.

'Hang on, I got a coupon!' a very shirtless Dean said as he ran up to the door waving a bit of paper. He grinned at Castiel as he handed it over. 'How you doing, mystery man?'

'I could tell you, but I'd have to kill you,' Castiel replied with a wink, and Dean nearly doubled over with laughter. 'With the coupon, that's twenty please.' The other guy pulled out the money, but Dean put a hand on his arm.

'Hey man, you don't have to pay.'

'Come on, Dean, I asked you out, I pay. You can get it next time.' He handed Castiel the original amount to include a tip and took the pizzas from him with a nod before heading back into the apartment. Dean didn't follow immediately, so Castiel made no move to leave.

'He doesn’t seem like your usual type,' Castiel said in what he hoped was a casual tone.

Dean shrugged. 'Variety is the spice of life.'

'At least he knows your name.'

Dean chuckled at that. 'Yeah, maybe I'll bust out the ropes tonight,' he said with a waggle of his eyebrows. 

'Just remember, safe, sane and consensual.'

Dean's eyes widened. 'Are, uh, are you really into that stuff, pizza man?' he asked softly.

That definitely hadn't been the reaction Castiel had been expecting. He raised a single eyebrow and replied firmly, 'You should address me properly. My name is Cas.' 

'Oh fuck,' Dean whispered, his cheeks going pink. Before he could say anything else, his date shouted that the pizzas were getting cold, and the spell was broken.

'Goodnight, Dean. Try not to get rope burn,' Castiel said imperiously before turning on his heel and walking back to his car. 

The façade collapsed once he was behind the wheel. All this time, he'd assumed that Dean was just being flirty as a joke, initially to deflect the awkwardness and after because it had become a bit of banter between them. But apparently Dean did actually swing that way and judging by the look on his face when Castiel had put on what Gabriel teasingly called his dom brow, the flirting had apparently been more serious than he'd realised.

Well, great. He was only two hours into a five-hour shift, he had a boner, and the person he was particularly interested in helping him with that problem was currently eating pizza with a hot guy before getting tied up and god knew what else. With a sigh, he started up the Lincoln and drove off to pick up the next round of pizzas.

**********

Another Saturday, another delivery to Dean's place, but this time it was the man himself who opened the door, fully dressed for once and apparently alone.

'Hey, Cas,' he said with a shy smile. 'How's it going?'

'Oh, um, fine, how are you, Dean?'

'Can't complain. Busy night?'

'The usual. What about you? No date?'

Dean rubbed the back of his neck, a hint of pink creeping onto his cheeks. 'Nah. Thought I'd have some me-time tonight.' He looked up at Castiel through his eyelashes and added with a cheeky grin, 'Unless you wanna split that pizza with me.'

'Unfortunately, I still have three more hours in my shift,' Castiel replied apologetically. 

'Too bad. Maybe next time.' He handed Castiel a twenty and brushed off his attempt to give change. 'See ya next week?'

'Of course. Goodnight, Dean.'

This time as Castiel walked to his car, his stomach felt full of butterflies instead of lead. There was no date! And Dean had sorta, kinda, in a way asked him out, or asked him in, or something. Maybe next week, if Dean still had no date over, Castiel would write his phone number on the pizza receipt and see if Dean called. Yes, that was exactly what he would do. 

Except the following Saturday, there wasn't an order from Dean at his usual time. Castiel did two rounds of deliveries, and still nothing, then a third round, but still no order from Dean. As the end of his shift approached, he resigned himself to what was clearly a rejection as he returned to the restaurant for the last set of pizzas.

'Got just one more for you, Cas. Asked for you by name.' Gabe handed him the pizza. 'Feel free to go home afterwards, we're wrapping up for the night.'

'OK, thanks Gabe. Goodnight.' When he picked up the delivery note, he was glad that his back was already turned, because no way would Gabe have let him leave without explaining the huge smile that had suddenly appeared on his face.

It was Dean's order. 

And he had asked for Castiel by name. 

At what he knew would be the end of his shift. 

Castiel may have been going a few miles over the speed limit on his way there.

When he knocked on the door, Dean answered wearing a robe. 'Hey Cas. Thanks for coming so late.'

'No problem. You're my last delivery.'

'Yeah, about that.' Dean bit his lip and played with the frayed end of the robe's belt. 'I, um… I kinda don't have any money for it.'

'I'm sorry?'

'Yeah, uh, turns out I must've lost my wallet or something. I don't have any cash or anything to pay for the pizza.' He looked at Castiel through those damn eyelashes again, a blush bringing out his freckles. It stirred something in Castiel, who honestly couldn't care less about the fifteen bucks Dean owed him right now.

'Well, Dean,' he replied with a low grumble in his voice, 'that just isn't acceptable. Whatever will we do with you?'

'I'm sorry, sir.' Dean ducked his head, and suddenly Castiel's jeans were a little too tight. He crowded into Dean's space, forcing him to back into the apartment and following him through the door and kicking it shut on the way.

'I'm afraid you're going to have to figure out another way to pay for this pizza, Dean.' Castiel couldn't believe that he had actually said those words, but the setup had just been too perfect. 

Apparently, Dean agreed, because he smiled widely. 'I was hoping you'd say that.' With a light tug, the belt of the robe came undone, and Dean shrugged it off his shoulders to let it pool at his feet. And underneath…

'Are those panties?' Castiel asked, voice even huskier as his desire took over. Dean just nodded, running a teasing finger along the satiny fabric where it was strained and damp over his hard cock. 'Fuck. Pink is definitely your colour.'

'Thanks. I was hoping you'd like 'em.' He took a step closer, looking almost shy. 'You _do_ like 'em, right?'

'Oh, I like them,' Castiel assured him. 'Very much.' He set the pizza down on the dining room table and noticed that there was a cushion on the floor next to one of the chairs. He looked at Dean with a raised eyebrow. 'What's this, Dean?'

'Um, I thought you might want to eat the pizza.'

'On the floor?'

Dean ducked his head. 'That's for me.'

'Pizza isn't ideal for hand-feeding.'

'I already ate.' He looked at Castiel as if willing him to understand his meaning so he wouldn’t have to spell it out.

'So while I eat, you want to kneel on the floor between my- oh, I see.' Dean smirked as he kneeled on the cushion, and Castiel couldn't deny that it was a tempting sight. He sat on the chair and bracketed Dean with his legs. 'What do you want, Dean?'

'Kinda obvious, isn't it?'

Castiel put a hand to Dean's cheek and made him look up. 'I never see the same date here twice.'

'None of them held my interest,' Dean shrugged.

'And me?'

'Heavenly Pizzas isn't _that_ good, Cas. I used to get it maybe once a month before you started delivering.'

That was all the answer Castiel needed. He leaned down and pressed his lips to Dean's, intending to keep it relatively chaste, but Dean had other ideas. He responded enthusiastically, thrusting his fingers into Castiel's hair and moaning when the kiss turned open-mouthed and frantic. Castiel pulled back first, enjoying the whimper that escaped Dean's throat. When he looked down, he could see that the panties were even damper and more stretched than before, and his own situation wasn't much better.

'You're beautiful,' Castiel murmured, running his thumb along Dean's lips. 'I was so disappointed when I didn't get your order at the usual time. I thought you didn’t want… pizza anymore.'

'I've been thinking about… pizza non-stop for weeks,' Dean replied teasingly. 'There is a lot of pizza man porn out there, and I'm pretty sure I've watched all of it.'

Castiel grabbed Dean by the chin roughly, satisfied at the little whimper that tore from Dean's throat. 'It sounds like you've been very naughty, Dean. Have you been thinking about me when you watched that porn?' Dean nodded. 'Did you touch yourself?' Another nod. 'And when you were with all those dates, were you thinking about me?'

Dean blushed but eventually nodded. 'Yeah. Thought about you all the time, Cas.'

'And what did you imagine, Dean?'

Dean rubbed Castiel's thighs, running his hands up and down, higher each time. 'Thought about sucking your cock. Just pulling you in the door and gettin' on my knees.' He licked his lips as he eyed the bulge in Castiel's pants. 'Thinkin' about it right now, actually.'

'Well, since you’ve been thinking about it for so long…' Dean grinned and reached up, making swift work of the button and zipper. Castiel stood to let Dean pull his pants and boxers down, but before he could sit again, Dean had swallowed him down to the root. 'Fuck!' Dean just hummed and smirked around Castiel's cock, working it like a porn star in one of the pizza man videos he'd mentioned. Castiel idly wondered if they'd watched any of the same ones, because yes, he may have indulged in the same activity a time or twelve himself. He stopped thinking anything when he felt Dean swallow around the head of his cock, and with little warning he cried out and came down Dean's throat.

He really hadn't intended to come so soon, but Dean's smug expression told him that Dean didn't mind. 'I guess you liked that, didn't you, sweetheart?'

'I did,' Castiel admitted, 'but I also didn't want to come yet. That was another naughty thing you did, Dean.'

Dean ducked his head and looked up from under his eyelashes. 'Are you gonna punish me?' he asked coquettishly. 

'Yes, I am.' He sat back down and pulled Dean over his lap, running a hand over his ass. 'Is this what you need? A firm hand?'

'Yes, sir.' Dean squirmed in Castiel's lap, the pre-come soaking his panties smearing onto Castiel's thigh. 'Please, sir.'

'Perfect,' Castiel murmured and smacked his hand down flat on Dean's left ass cheek. Dean gasped, his eyes fluttering shut. Castiel alternated between left and right, turning the pale skin of Dean's ass bright red with just a dozen blows. Dean was a trembling mess, hard as a rock, breathing shallow and rubbing himself against Castiel's thigh. Castiel massaged the hot skin and slipped his hand under the panties to gently rub away the sting. Dean moaned deliciously. 'God, you're gorgeous.'

'Do you wanna fuck me?' Dean asked breathlessly.

'I would very much like to do that.' He helped Dean to his feet before pulling up his pants and letting himself be led by the hand to Dean's bedroom. The metal-framed king size bed looked extremely inviting, particularly with the candles on the nightstands and the bondage ropes attached to the four corners of the bed frame. 'I guess you were feeling optimistic?'

'I saw the way you looked at me last week,' Dean replied with flirty bravado, and got another spank for his brattiness. 'And I hoped you saw the way I looked at you,' he added more genuinely.

'I did. I pictured it every time _I_ watched pizza man porn,' Castiel admitted as he ran a fingertip up and down Dean's hard length. The panties were well and truly soaked, and the head of Dean's cock peeked out over the lacy waistband. 'But you are much more appealing than the "barely legal" babysitters who usually featured in those scenes.' Dean's laugh at Castiel's use of air quotes turned into a moan when the light fingers over the panties turned into a firm squeeze. 'Although, like you, they also needed to be spanked. I guess they too must have done something wrong.'

'How about I get on my hands and knees and make it right for you, sweetheart?'

Castiel kissed along Dean's neck and jaw, stopping to whisper in his ear. 'I want to see your face when you come.' Dean shuddered, his cock throbbing in Castiel's grip. 'Give me lube and a condom, then lie on your back for me.'

'Fuck yeah.' Dean turned to the nightstand nearest the door and rummaged around until he found the requested items before throwing himself onto the bed and lying spread-eagle with a goofy grin on his face. 'You wanna tie me up?'

Castiel smiled as he stripped down to nothing. 'Maybe next time. Tonight I want you to be able to touch me.' He straddled Dean's bowlegs, again running his hand over the front of the panties. 'How attached are you to these?'

'Got half a dozen more just like 'em,' Dean replied with a gasp.

'Good. Because I plan to ruin them.' As Dean moaned his approval, Castiel kissed his way down Dean's body until he got to the panties. Without taking Dean's cock out, he licked and sucked along the length, soaking the panties further and turning Dean into a begging mess. As his own impatience and, by some miracle, his second erection, was growing, Castiel took pity on Dean and reached for the lube. He slicked up his first finger and slipped it beneath the elastic without bothering to remove the panties. Apparently, Dean had been anticipating this as well, because Castiel's finger slipped right in. 'You started without me.'

'What can I say? I was a Boy Scout.'

'Were you eager for my cock, Dean?' Castiel asked in a voice somehow even deeper than usual.

'Fuck yeah, Cas. Been wanting it. I prepped real good, you can just go for it.' Castiel tested the assertion by adding two more fingers, and sure enough, Dean could take them without difficulty. A third slid in with equal ease, and Castiel teased at Dean's prostate to extract another delicious moan from him. 'Come on, Cas, please.'

Seeing no need for further delay, Castiel opened the condom and put it on, slicking himself up before nudging at Dean's entrance. 'Ready for me?' Dean nodded vigorously, wiggling his hips to encourage Castiel to hurry up. That earned him another smack to the ass, but Castiel was also done waiting. He pushed inside smoothly with a sigh of contentment. 'Oh fuck, you feel so good.' He presumed Dean's moan to be one of agreement.

They started slowly—Castiel wanted to savour the feeling, and Dean didn't get much choice in the matter lying on his back with his bowlegs wrapped around Castiel's waist. After a few minutes of slow thrusting and changing angles until he found the sweet spot to hit Dean's prostate, Castiel put one leg up on his shoulder to give him better leverage. Dean's back arched as he grabbed the bars above his head. The pace increased, sweat glistened on Castiel's tan skin, and the blush bringing out Dean's freckles spread from his cheeks to his chest. 

'Touch yourself, Dean. I want to see you come for me,' Castiel panted when he knew was getting close. Dean obeyed quickly, reaching into the panties and jerking himself off with clear desperation while Castiel continued to pound into him. He came with a long moan less than a minute before Castiel reached his own climax.

'Son of a bitch,' Dean huffed when he was able to draw breath. 'That was fuckin' awesome.'

'I agree. Who knew pizza delivery could be such an exciting career?' 

'It's important to learn something new every day, pizza man,' Dean replied with a grin.

'I agree with that, too. And what have you learned from the pizza man, Dean?' Castiel asked seductively, dipping a finger into the ruined panties to have a taste of Dean's come.

Dean shuddered as his dick made a valiant attempt to perk up again. 'I think I'm about to learn how short I can get my refractory time.'

'That sounds like a very intriguing scientific question,' Castiel agreed. 'I'll be your lab assistant.'

**********

Castiel woke up the next morning to a disappointingly empty bed, but the nightstand had a large thermal cup full of coffee and a doughnut sitting on it, and underneath was a note.

_Morning sunshine! Sorry I had to leave early for work, but if you don't mind hanging around, I should be back by 3. If you don't have time to wait, my number is on the pizza receipt. Maybe we could see each other again before next Saturday? -Dean_

The pizza receipt was under the note, with Dean's number circled in red pen. Underneath it was another circle, and Castiel laughed for a solid minute when he realised that this one pointed out a crucial detail he had failed to notice the night before. 

_Paid by card._


End file.
